


Double, Double (Minus the Toil and Trouble)

by AngeNoir



Series: Write-Away Giveaway Fills on Tumblr [12]
Category: Supernatural
Genre: F/F, M/M, Post Finale, Post Season/Series 08 Finale, double-date
Language: English
Status: Completed
Published: 2013-05-25
Updated: 2013-05-25
Packaged: 2017-12-12 22:26:34
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,496
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/816753
Author URL: https://archiveofourown.org/users/AngeNoir/pseuds/AngeNoir
Summary: <blockquote class="userstuff">
              <p>Sam, apparently, really needs to teach Dean how to date when it comes to someone he really cares about. Charlie is enlisted to help.</p>
            </blockquote>





	Double, Double (Minus the Toil and Trouble)

**Author's Note:**

> As a celebration for reaching 100 followers on tumblr, I held a giveaway, and what I gave away is prompt fills for anyone who asks! I received this prompt from [gwenwinin](http://gwenwinin.tumblr.com):
> 
>  
> 
> _Destiel go on a double-date. (I would like Charlie to be involved)._
> 
>  
> 
> I WILL SAY THIS: the last episode I watched was the French Mistake, back in season 6. I have been unable to keep up with the seasons. Therefore, this is going to be a bit (or a lot) OOC for the season, and there are (most likely) probably going to be mistakes in details. If you let me know, I can correct them!

“He’s just going to – he just needs a little push, that’s all.”

Charlie hummed under her breath as she debated between blueberry and strawberry yoghurt. She liked blueberry more than strawberry, but strawberry was Kendra’s favorite…

“Charlie, it’s really starting to bug me. It’s obvious during the best of times and stifling during the worst.”

She didn’t know much about the brothers, but Sam seemed desperate in a way that did not coincide with ‘wanting his big brother to get laid.’ “What else is going on?” she asked.

There was a pause on the phone, and then Sam snorted. “Nothing. Why?”

She might not have been a big sister, but she’d played the innocent often enough to recognize the lie. Tossing the strawberry into the cart, she pushed on to the meat substitute isle. “Because you wouldn’t be calling me if you didn’t need help.”

For a moment, she thought Sam might have hung up on her – certainly enough time passed that she moved from the frozen foods’ aisle to the kitchen cleaners’ aisle. Finally, Sam let out a long, almost defeated-sounding, sigh. “He needs help, Charlie. You haven’t seen him around this guy. He really – he really wants to go for this, I think, but he’s still trying to come to grips with it. And I just want to help… ease that along. Somehow.”

“I still fail to see how that involves me. And it sounds a lot more serious than what you just described.” Picking up the bottle of eco-dishwashing fluid, she dumped it in the cart and moved towards checkout. “You sound really freaked out, which is making me freaked out, because you guys rarely sound freaked out. You always know what you’re doing.”

Sam laughed weakly, the sound distorted and broken by the electronics of the phone. “No, Charlie, not much more serious. I just – I want this to go right for him. I want him to have this go right for him. He deserves it.”

Charlie placed the items in her cart up on the conveyer belt, smiling at the woman at the cash register. “Well, if you aren’t going to tell me what’s wrong, go ahead and tell me what you need help with. Or what Dean needs help with, rather.”

There was no sound at all, and then Sam cleared his throat. “Just – bear with me,” Sam said, and then he heaved a deep breath. “I need you to help him go on a date.”

“What?!” Charlie gasped, and the cashier looked at her worriedly. Waving her hand in a no-everything’s-okay way, Charlie tugged the phone closer to her mouth and hissed, “How am I supposed to do _that_?”

“Well, he’s been wanting to check up on you,” Sam said earnestly. “I’ll just send him down with the guy that he wants to be dating but isn’t sure how to date, and you just… take him on an activity that would be date material. With your own date, of course. Your last email said you had someone – Linda?” He paused, and then corrected himself before she could. “Kendra, right?”

“And I’m just supposed to trick him into doing this?” she demanded, wheeling the cart out of the store with the bagged groceries.

“Well.” Sam cleared his throat and she could almost see him apologetically shrug. “Yes and no? When he shows up, just tell him it’s date night. And that he’s welcome to tag along and just hang. With his best friend. Who he’s been pining over for a long while.”

With a sigh, Charlie closed the trunk and shoved the cart into the little cart-corral place. “Alright. Well. You sure there’s nothing else you wanna tell me?”

“I’m sure,” Sam said.

She was certain she was missing something – there was something off with his voice – but she wasn’t going to pry. Maybe something really bad happened.

* * *

 

When the doorbell rang, she wasn’t as surprised as she might have been when she opened it to find Dean standing in the doorway. Before he could even open his mouth to say anything, she launched herself at him and gave him a tight hug.

His arms came up, wrapping around her shoulders, and she could almost _feel_ the tension leave his shoulders. “Hey there,” he said in that rough accent, and she didn’t even know why, but tears pricked the corners of her eyes.

“Hey,” she said softly, before stepping back to get a look at his companion.

“Ah, Charlie, meet Cas. Castiel. He’s, ah. Where’s your girl?”

“Upstairs – we’re getting ready for date night,” Charlie said, remembering her conversation with Sam earlier. “Gonna go watch the new Iron Man movie.”

Dean winced a little. “Ah, I was hoping to just – check up on you. See how you’re doing. If you’re busy, I can—”

“No!”

Dean paused, frowning. “No?”

Desperately casting her mind around for a good excuse, Charlie blurted out, “I would like for you to come along!”

Dean cocked his head at her suspiciously. “On your _date night_?”

“Well, yeah! I mean – I want to talk with you, too. And you can bring Cas along, too. I’m sure he’d love the movie!”

“Charlie, babe, who are these hunks?”

Kendra’s voice never failed to make Charlie relax, and she turned with a warm smile as her girlfriend sauntered over, one eyebrow lifted at their guests. “These are – this is Dean and Cas. Remember I said we’d have a double-date?”

That made Dean frown, but Cas suddenly smiled. “I would like that,” he said softly.

Dean started in surprise at that. “Really?”

Cas nodded quietly, and after a moment, Dean sighed. “Okay. Well. If you guys don’t mind us interrupting your date – “

“Oh, you won’t be interrupting,” Kendra assured them easily. “And you can talk afterwards. We can get a late dinner. C’mon, gorgeous, you can escort me to the car.”

Cas blinked, taken aback when Kendra grabbed his arm, but obligingly led her down the path.

“We’re taking the same car?” Dean asked, lifting an eyebrow.

Charlie squirmed.

Heaving a sigh, Dean rubbed his face. “Sam put you up to this, didn’t he?”

“…Kinda?”

Grumbling under his breath about interfering younger siblings, Dean slung an arm around her shoulders and guided her down the path. “How much can I speak about what I do in front of your girl?” he asked quietly.

“Um… I think everything? She, um. I met her online. She knows about these kind of things. Kinda. Like. Her mom and dad were killed by some monster. Her older sister got into hunting. She never did.”

Dean’s mouth quirked, a little bitterly. “Smart girl,” he murmured, even as he made a face at Charlie’s car. “I’m gonna have to squeeze in the back with Cas, aren’t I?”

“Think of it as an early start on your date!” Charlie replied brightly.

Groaning under his breath, he dropped his cheek on top of her head and just held her. She was surprised how much he seemed to need it – and how much it warmed her, to be held like that. He was close to the older brother she never had, warm and strong and dependable. “I’m glad you’ve been okay, Charlie,” he whispered into her hair, before letting her go and clambering into the backseat.

* * *

 

Sam smiled as he read Charlie’s email – a long, rambling composition, spattered with liberal exclamation points and also deep discussions about the representation (or, more accurately, lack of representation) of powerful females within the medieval comic genre and the latest happenings at her job. There was a paragraph in there, about sitting through Iron Man 3, which had apparently been torturous for Dean, though Cas had been enraptured by it. They’d gone out to eat afterwards, discussing protection methods and just life in general. Dean had apparently grown more and more comfortable with Cas by his side, and Cas more and more tactile as the night had progressed and he grew more comfortable as well.

_“I really think you’re right – he’s pining, but Cas seems to get that, too, and he’s giving all the right signals. I think even Dean was satisfied with the date, that it went well. If you ever want me to help in that same way again, though, do it in a less obvious way. Dean was on me before we even walked out the door._

_“Don’t forget you owe me! Even if it was pretty awesome. You should come along next time – it wasn’t over-couple-y the way things can be, sometimes. It’d be good to see you again.”_

With a sad smile, Sam closed the email and sighed, trying not to notice how much his hands were shaking and how much pain he was in. He was very glad that Dean was finding a good friend and even lover in Cas.

Sam wasn’t certain how long he’d be around, in any case. Dean needed someone to be there for him when this last, aborted trial finally took Sam’s life.


End file.
